For eight months during the end of Pontiac's War, Conococheague settlers prevented traders from bringing illegal arms to enemy Indians and they confronted the British soldiers, who aided the traders, at Fort Loudoun. Their uprising included protests, attacks on packhorse trains by the disguised "Black Boys," a kidnapping, a gunfight, and a siege at Fort Loudoun by hundreds of armed men. There were at least seven shooting incidents, comprising hundreds of shots fired in anger. Many of the Conococheague settlers were of Scots-Irish decent and the British soldiers they were fighting, who were holed up in Fort Loudoun, were the Scottish, 42nd (Royal Highland) Regiment of Foot – their “cousins.” “Of foot” means an infantry regiment.

mid-1763 - James Smith forms and leads Conococheague rangers, preventing local raids until disbanded when funding stops. James Smith joins John Armstrong's regiment, which campaigns to Indian sites along the Susquehanna River's West Branch in the fall

Nov 1764 - George Croghan, Robert Callender and Philadelphia merchants make a secret agreement to provide £20,000 worth of trade goods to the western In¬dians, far exceeding the £2,000 General Thomas Gage (commander of British troops) allotted Croghan for Crown presents to be given in peace negotiations

March - Local settlers know or suspect illegal gunpowder, lead, and weapons for Indian trade are stored at Pawling's Tavern (Howe's). Discovered scalping knives alarm locals

March 5 - Two trains of 32 and 59 packhorses with Indian goods, headed for Fort Pitt, leave Pawling's Tavern (with just a fraction of Callender's Indian trade goods)

March 5 - Groups of 30 to 50 armed protestors confront packhorse trains at William Maxwell's home, Cunningham's Tavern, William Smith's House and McConnell's Tavern. Packhorse drivers are threatened and guns fired

March 5 PM - James Smith gathers 10 of his former rangers and sets up ambush near Sideling Hill

March 6 1PM - Packhorse trains reach "within a mile or two" of Sideling Hill and are shot at by Smith's men disguised as Indians with blackened faces (hence, "Black Boys"). 2 to 4 horses killed. 59 to 63 (out of 81) loads of goods burned, worth £3,000 per one claim

March 7 AM - From midnight through morning, on way to Sideling Hill and back, troops have several angry confrontations with armed men in Larraby's (Cove) Gap and further up Tuscarora Mountain. Troops capture 6 locals and 9 guns. Troops search McConnell's Tavern and then retrieve rum and other undamaged goods from ambush site. Troops shoot at locals and use bayonets to clear mobs. Take captives, guns, and retrieved goods to Fort Loudoun

March 7 PM - Robert Callender and two others, accompanied by Justice James Maxwell, take Reese Porter from his house and hold him at Fort Loudoun with other prisoners

March 8 - Hundreds of Conococheague settlers arm and gather. They threaten the lives of Callender and Maxwell and prepare to rescue prisoners at Fort Loudoun

March 9 - 200 to 300 armed men, led by James Smith, confront Lt. Charles Grant and his troops at Fort Loudoun. Grant releases his prisoners on bail, but keeps confiscated guns.

March 9 - Black Boys search for ammunition at Pawlings Tavern. Finding none, they go in blackened-face disguise to William Maxwell's house, where they find and blow up 8 barrels of gunpowder

March - Robert Callender moves remaining Indian trade goods stored at Pawlings Tavern, William Maxwell's, and other nearby houses to Fort Loudoun

March-July - Black Boys set up patrols on roads in Conococheague Settlement. Inspect both private and military groups to prevent shipment of Indian trade goods. Issue passes to allow approved material to proceed. William Smith's house and Cunningham's Tavern serve as the central meeting places for the Black Boys during this period

March - Cumberland Valley inhabitants petition Gov. John Penn to keep and enforce his ban on "warlike stores" to Indians. Express fear of third Indian war if Indians are re-armed

Mar-April - General Thomas Gage (commander of British troops) and Sir William Johnson (head Indian agent) investigate and disapprove of George Croghan and his associates shipping more Indian goods than authorized

March - Gov. John Penn and his Attorney General go to Carlisle to investigate and indict those involved in the Sideling Hill ambush. Some depositions and arrest warrants made, but suspected "robbers" and "rioters" hide from sheriff and "three Presbyterian parsons."

May 6 - At Widow Barr's place, 50 to 80 Black Boys (those at Harris's joined by others from Cunningham's Tavern) surprise and shoot at troops, starting a gunfight. Black Boy James Brown is shot in the thigh. Sgt. McGlashan takes one prisoner and uses Widow Barr's house as a fort. Troops are allowed to leave when they give up their prisoner. Black Boys proceed back to Cunningham's Tavern.

May 10 - 150 to 200 armed men led by James Smith, and Justices William Smith, John Allison and Reyonald, arrive at Fort Loudoun and demand to inspect and take inventory of the Joseph Spear's goods stored there. Lt. Grant refuses to let them inspect the goods, fearing that the men intend to destroy the goods instead. Justices say they have no regard for military passes and that all goods required passes from magistrates. Protestors leave peacefully

May - Black Boys continue to inspect private and military shipments on local roads and issue passes for approved goods. William Smith's house and Cunningham's Tavern are still the common rendezvous for the Black Boys

May - George Croghan holds peace conference with more than 500 Ohio Indians at Fort Pitt. Indians renew their peace promises and Shawnees release their remaining white captives. Croghan reports this to Gov. Penn and others before heading down the Ohio River to reach peace agreements with Illinois Indians and Pontiac

May 8 - Ohio Delawares formalize peace agreement with Sir William Johnson in New York

May 28 - James Smith and four others kidnap Lt. Grant while riding a mile from Fort Loudoun. They hold Grant captive in the woods overnight

May 29 - Smith and others release Grant after he signs a £40 bond securing he will return the 9 guns collected after the Sideling Hill ambush. But Grant does not return the guns

May 29 - Fort Loudoun commissary, Thomas Romberg, claims to have found and made a copy of an inflammatory advertisement supposedly recruiting men to the Black Boys and saying their church and governor will pardon their misbehavior and crimes

May or June - 2 officers and 45 men march from Fort Pitt toward Fort Loudoun to rescue the kidnapped Lt. Grant. They turn back on way with the news that Grant had returned

May or June - Justice William Smith issues a warrant for the arrest of Sgt. McGlashan for shooting James Brown at Widow Barr's

June 4 - Based on news of Indian peace agreements and the Shawnees' return of white captives, Gov. Penn repeals Indian trade restrictions, effective June 20, 1765

June 7 - Report of attack by "Cumberland County inhabitants" on goods sent by Joseph Spear, but location not stated. Black Boys store and then burn these goods

June 16 - Gen. Thomas Gage writes to Gov. Penn: "the Inhabitants of Cumberland County . . . appear daily in Arms, and seem to be in an actual State of Rebellion. It appears, likewise, that the Rebels are supported by some of the Magistrates, particularly one Smith, a Justice of the Peace, and headed by his Son [i.e., his brother-in-law James]"

June 27 - Gov. Penn summons William Smith to meet with him in Philadelphia on July 30th

June 27 - Gov. Penn writes to the justices of Cumberland County sending copies of Romberg's advertisement and orders that they "quell and suppress the first appearances of any riots & disorders in the County, to preserve the publick peace, & to bring the Offenders to Justice." Orders a report of affairs, particularly concerning Lt. Grant's kidnapping

Summer George Croghan reaches peace agreements with Illinois and Great Lakes Indians and Pontiac. (Final peace agreement between Sir William Johnson and Indians is made at Fort Ontario in July 1766)

July-Oct- Black Boys stop their inspections of shipments and cease confrontations with troops

July 18 - Cumberland County Magistrates meet at Fort Loudoun in response to Gov. Penn's letter. No arrest warrants issued by them

July 30 - Justice William Smith defends himself before Gov. Penn saying that Lt. Grant illegally interfered with the civil law and took bribes from Robert Callender. Smith retains his magistrate position

Aug 24 - Lt. Grant writes to Gen. Gage defending his actions and asking for guidance on what to do with the 9 guns confiscated after Sideling Hill ambush. He notes that William Smith "Stands in a fair light with the Governor"

November - Garrison at Fort Loudon prepares to abandon Fort Loudoun and move to Fort Pitt. Black Boys are resentful that their 9 guns are still confiscated and fear that Lt. Grant will take them away. The Fort Pitt commander sends an ensign and 30 troops to escort the Fort Loudoun troops west

Nov 16-18 - 100 to 200 armed Black Boys surround Fort Loudoun and demand the return of the 9 guns. For 2 days and 2 nights they fire hundreds of shots at the fort and its sentries

Nov 18 - Lt. Grant agrees to give the 9 guns to Justice William McDonnell under bond, with the agreement he holds them until "the Governor's pleasure is known". (The Governor later directed that the guns be given back to their owners.) James Smith and others sign bond in which they agree not to attack the troops further. Troops from Fort Pitt arrive 2 hours later and peacefully escort the Fort Loudoun garrison away. This marks the end of the 8-month Conococheague Uprising of 1765

Aftermath

Jan 1766- Gov. Penn removes William Smith as a magistrate and issues a writ for the arrest of James Smith

1766 - Merchants still fear attack by Black Boys but none come. James Smith and other Black Boys are never arrested

June 1766 - James Smith leaves Conococheague to explore Tennessee and Kentucky